ALCAZAR JIMENEZ, JACKSON JOSE
Preferred name
ALCAZAR JIMENEZ, JACKSON JOSE
Main Affiliation
Email
jackson.alcazar@udd.cl
ORCID
0000-0002-6300-6923
Scopus Author ID
56976043600
13 results
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Item type:Publication, Influence of β-Cyclodextrin Methylation on Host-Guest Complex Stability: A Theoretical Study of Intra- and Intermolecular Interactions as Well as Host Dimer Formation(2023); <jats:p>Understanding the non-covalent interactions in host-guest complexes is crucial to their stability, design and applications. Here, we use density functional theory to compare the ability of β-cyclodextrin (β-CD) and heptakis(2,6-di-O-methyl)-β-cyclodextrin (DM-β-CD) to encapsulate the model guest phenol. For both macrocycles, we quantify the intramolecular interactions before and after the formation of the complex, as well as the intermolecular host-guest and host-host dimer interactions. These are individually classified as van der Waals interactions or hydrogen bonds, respectively. The results show a stronger intramolecular binding energy of β-CD, with the absolute difference being −5.53 kcal/mol relative to DM-β-CD. Consequently, the intermolecular interactions of both cyclodextrins with phenol are affected, such that the free binding energy calculated for the DM-β-CD/phenol complex (−5.23 kcal/mol) is ≈50% more negative than for the complex with β-CD (−2.62 kcal/mol). The latter is in excellent agreement with the experimental data (−2.69 kcal/mol), which validates the level of theory (B97-3c) used. Taken together, the methylation of β-CD increases the stability of the host-guest complex with the here studied guest phenol through stronger van der Waals interactions and hydrogen bonds. We attribute this to the disruption of the hydrogen bond network in the primary face of β-CD upon methylation, which influences the flexibility of the host toward the guest as well as the strength of the intermolecular interactions. Our work provides fundamental insights into the impact of different non-covalent interactions on host-guest stability, and we suggest that this theoretical framework can be adapted to other host-guest complexes to evaluate and quantify their non-covalent interactions.</jats:p>5Scopus© Citations 10 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, Reliable and accurate prediction of basic pKa values in nitrogen compounds: the pKa shift in supramolecular systems as a case study(2023); 4Scopus© Citations 10 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, Exploring the behavior of Candida antarctica lipase B in aqueous mixtures of an imidazolium ionic liquid and its surfactant analogue(2023); ; ; Limberg Jaldin<jats:p>The performance of <jats:italic>Candida antarctica</jats:italic> lipase B (CALB) has been evaluated in 1-butyl-3-methylimidazolium tetrafluoroborate (BMIMBF<jats:sub>4</jats:sub>)/water mixtures in a wide range of molar fractions (<jats:inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="m1"><mml:mrow><mml:msub><mml:mi mathvariant="normal">χ</mml:mi><mml:mrow><mml:mi>B</mml:mi><mml:mi>M</mml:mi><mml:mi>I</mml:mi><mml:mi>M</mml:mi><mml:mi>B</mml:mi><mml:mi>F</mml:mi><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow></mml:math></jats:inline-formula>) with and without 1-dodecyl-3-methylimidazolium tetrafluoroborate (C<jats:sub>12</jats:sub>-MIMBF<jats:sub>4</jats:sub>), a surfactant derived from BMIMBF<jats:sub>4</jats:sub>. The main aim of this work is to evaluate the influence of <jats:inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="m2"><mml:mrow><mml:msub><mml:mi mathvariant="normal">χ</mml:mi><mml:mrow><mml:mi>B</mml:mi><mml:mi>M</mml:mi><mml:mi>I</mml:mi><mml:mi>M</mml:mi><mml:mi>B</mml:mi><mml:mi>F</mml:mi><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow></mml:math></jats:inline-formula> over micellar aggregates to assess the activity of enzymatic reactions. The investigated reaction corresponds to the hydrolysis of the substrate <jats:italic>p</jats:italic>-nitrophenyl laureate in each <jats:inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="m3"><mml:mrow><mml:msub><mml:mi mathvariant="normal">χ</mml:mi><mml:mrow><mml:mi>B</mml:mi><mml:mi>M</mml:mi><mml:mi>I</mml:mi><mml:mi>M</mml:mi><mml:mi>B</mml:mi><mml:mi>F</mml:mi><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow></mml:math></jats:inline-formula>. The kinetic study for <jats:inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="m4"><mml:mrow><mml:msub><mml:mi mathvariant="normal">χ</mml:mi><mml:mrow><mml:mi>B</mml:mi><mml:mi>M</mml:mi><mml:mi>I</mml:mi><mml:mi>M</mml:mi><mml:mi>B</mml:mi><mml:mi>F</mml:mi><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow></mml:math></jats:inline-formula> at around 0.2 proved to be a border point in enzymatic activity. At <jats:inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="m5"><mml:mrow><mml:msub><mml:mi mathvariant="normal">χ</mml:mi><mml:mrow><mml:mi>B</mml:mi><mml:mi>M</mml:mi><mml:mi>I</mml:mi><mml:mi>M</mml:mi><mml:mi>B</mml:mi><mml:mi>F</mml:mi><mml:mn>4</mml:mn></mml:mrow></mml:msub></mml:mrow></mml:math></jats:inline-formula> = 0.1, the lipase activity increases in the presence of C<jats:sub>12</jats:sub>-MIMBF<jats:sub>4</jats:sub>. However, at higher concentrations, BMIMBF<jats:sub>4</jats:sub> has a negligible effect over the lipase activity. These results suggest specific interactions between water and BMIMBF<jats:sub>4</jats:sub> molecules in relation to CALB. This research highlights the superactivity phenomenon driven by the reaction media and the micelle interface. In this interfacial interaction, BMIMBF<jats:sub>4</jats:sub> acts directly on the changes induced on the enzyme upon its interaction with the micellar interface. This study opens a green perspective toward the biocatalysis field.</jats:p>12Scopus© Citations 4 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, A Simple Machine Learning-Based Quantitative Structure–Activity Relationship Model for Predicting pIC50 Inhibition Values of FLT3 Tyrosine Kinase(MDPI AG, 2025-01-14); 8Scopus© Citations 19 - Some of the metrics are blocked by yourconsent settings
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Item type:Publication, Thiophene Stability in Photodynamic Therapy: A Mathematical Model Approach(2024)<jats:p>Thiophene-containing photosensitizers are gaining recognition for their role in photodynamic therapy (PDT). However, the inherent reactivity of the thiophene moiety toward singlet oxygen threatens the stability and efficiency of these photosensitizers. This study presents a novel mathematical model capable of predicting the reactivity of thiophene toward singlet oxygen in PDT, using Conceptual Density Functional Theory (CDFT) and genetic programming. The research combines advanced computational methods, including various DFT techniques and symbolic regression, and is validated with experimental data. The findings underscore the capacity of the model to classify photosensitizers based on their photodynamic efficiency and safety, particularly noting that photosensitizers with a constant rate 1000 times lower than that of unmodified thiophene retain their photodynamic performance without substantial singlet oxygen quenching. Additionally, the research offers insights into the impact of electronic effects on thiophene reactivity. Finally, this study significantly advances thiophene-based photosensitizer design, paving the way for therapeutic agents that achieve a desirable balance between efficiency and safety in PDT.</jats:p>8Scopus© Citations 6 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, Avibactam–Cyclodextrin Inclusion Complexes: Computational and Thermodynamic Insights for Drug Delivery, Detection, and Environmental Scavenging(MDPI AG, 2025-08-18); ; <jats:p>The escalating crisis of multidrug resistance, together with the persistence of antibiotic residues in clinical and environmental matrices, demands integrated strategies that couple sensitive detection, efficient decontamination, and controlled delivery. However, current techniques for quantifying avibactam (AVI)—a broad-spectrum β-lactamase inhibitor—such as HPLC-UV lack the sensitivity and specificity required for both therapeutic drug monitoring and environmental surveillance. Encapsulation of AVI within cyclodextrins (CDs) may simultaneously enhance its stability, bioavailability, and detectability, while the high binding affinities of CDs position them as molecular traps capable of scavenging residual AVI. In this study, the inclusion complexation of AVI with various CDs was examined through molecular dynamics (MD) simulations, experimental isothermal titration calorimetry (ITC), and non-covalent interaction (NCI) analysis. Stable 1:1 inclusion complexes were observed between AVI and β-cyclodextrin (β-CD), 2,6-dimethyl-β-cyclodextrin (DM-β-CD), and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), with standard Gibbs free energies of binding (ΔG°) of –3.64, –3.24, and –3.11 kcal/mol, respectively. In contrast, γ-cyclodextrin (γ-CD) exhibited significantly weaker binding (ΔG° = –2.25 kcal/mol). DFT-based NCI analysis revealed that cooperative interaction topology and cavity complementarity, rather than the sheer number of localized contacts, govern complex stability. Combined computational and experimental data establish β-CD derivatives as effective supramolecular hosts for AVI, despite an entropic penalty in the DM-β-CD/AVI complex. These CD–AVI affinities support the development of improved analytical methodologies and pharmaceutical formulations, and they also open avenues for decontamination strategies based on molecular trapping of AVI.</jats:p>1 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, Linear relationship between emission quantum yield and Stokes shift in 3-styryl aza-coumarin based dyes in the presence of cyclodextrins(2023); 1Scopus© Citations 8